Cellulose organic acid ester plastics containing resacetophenone



Patented Jan. 29, 1946 CELLULOSE ORGANIC ACID ESTER PLAS- TICS CONTAINING RESACETOPHENONE Lester W. A. Meyer and William M. Gear-hart, Kingsport, Tenn., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing.

3 Claims.

This invention relates to cellulose organic acid ester plastics, and more particularly to the stabilization of such plastics.

As iswell known in the art, plastics having excellent properties for a great many purposes can be prepared from cellulose organic acid esters, such, for example, as cellulose acetate, cellulose propionate, cellulose butyrate, cellulose acetatepropionate and cellulose acetate-butyrate, with suitable plasticizers. Many examples of suitable plasticizers are shown in the art. The choice of plasticizers forms no part of our invention.

However, cellulose organic acid ester plastics have not been entirely suitable for use in places where they are exposed to a considerable amount ofultra-violet light: e. g., out of doors. After one or two months of outdoor exposure in a sunny climate, the plastic bleached and became increasingly brittle until, at the end of from three to six months, depending on the severity of the climate, crazing occurred. The rapid deterioration of appearance was accompanied by an equally rapid breakdown in physical properties, such as strength.

Some compounds whose addition to the plastic composition inhibited physical breakdown of the plastic, caused intense discoloration when the plastic was exposed for any length of time to sunlight or other source of ultra-violet light.

We have found that the addition of a small proportion of resacetophenone acyl groups contain from 2 to 4 carbon atoms.

In testing our cellulose organic acid ester plastics containing resacetophenone, we have employed outdoor exposure in Arizona, Florida, and Tennessee, as well as an accelerated weathering test in the Kline sunlight-fog chamber. This test is described in section B-14 of the Federal Specification for Plastics, Organic; Genera1 Specifications (Methods of Tests) L-P-406 or L-P-406a, published by the U. S. Treasury Department, Federal Specifications Division. Two

Application February 28, 1945, Serial No. 580,285

hundred hours under this test has been found to be roughly equivalent to one year of weathering in Washington, D. C. However, the climates of Florida and Arizona are much more severe as to ultra-violet light than the climate of Wash ington, D. C. In the Kline accelerated test, when samples 0.050-0.075" thick are used, the bleaching-brittleness stage of a plasticized cellulose organic acid ester plastic containing no ultraviolet inhibitor is reached in about -200 hours. Grazing occurs in 200-250 hours exposure, although occasionally 300 hours is reached without crazing, but with the development of brittleness. Similar samples of plasticized cellulose organic acid ester plastics of the same compositions, but containing in addition 1% (based on the weight of cellulose ester) of resacetophenone, withstood more than 800 hours in the Kline accelerated test before failing. correspondingly favorable results are indicated by the progress of outdoor exposure tests.

Resacetophenone is advantageously introduced into a cellulose organic acid ester plastic at the time the cellulose ester is compounded with the plasticizer. This compounding may be accomplished by anyof the known methods, including the method of working on hot rolls described in Conklins U. S. Patent 2,155,303. Resacetophenone causes no substantial discoloration of the plastic, even when the hot-rolling method of compounding is employed, and no substantial discoloration takes place during either outdoor exposure or accelerated testing.

By way of illustration, we give the following examples of making up cellulose organic acid ester plastics containing resacetophenone. It will be understood that these illustrations do not constitute a limitation of our invention, which is defined in the appended claims.

Example 1.480 g. of cellulose acetate-butyrate containing approximately 12 /270 acetyl and 37% butyryl, 40 g. of triphenyl phosphate, and 9.6 g. of resacetophenone are dissolved in a mixture of 1640 cc. of ethylene dichloride and 288 cc. of

' methanol. A sheet is formed from the resultin dope by spreading it on a smooth surface and allowing the solvent to evaporate.

Example 2.--l00 parts by weight of cellulose acetate butyrate containin approximately 12 /2% acetyl and 37% butyryl, 14 parts by weight of dibutyl sebacate, and 1 part by weight of resacetophenone are worked together on hot rolls by the method described in the Conklin Patent 2,155,303. Sheets are rolled from the plastic mass thus obtained.

Example 3.Cellulose. acetate is substituted for the cellulose acetate-butyrate of Example 2.

Any of the known plasticizers for cellulose organic acid esters, such, for example, as dibutyl phthalate, dibutyl sebacate, methoxy-ethyl stearate, tricresyl phosphate, butoxy-ethyl phthalate, diamyl phthalate, ethyl p-toluene sulfonamide, etc. may be used. In the case of the softer cellulose esters, such as cellulose acetate-butyrate, plastics may even be formed without the use of any plasticizer. v a

What we claim as our invention and desire to be secured by Letters Patent of the United States 151 1. A cellulose organic acid ester plastic comprising a cellulose organic acid ester whose acyl groups contain from 2 to 4 carbon atoms, a plasticizer therefor, and, as an agent for inhibiting 15 acetophenone.

deterioration of the plastic by ultra-violet light. approximately 1%2%, based on the weight of the cellulose ester, of resacetophenone.

2. A cellulose acetate-butyrate plastic comprising cellulose acetate-butyrate, a, plasticizer therefor, and, as an agent for inhibiting deterioration of the plastic by ultra-violet light, approximately 1%-2%, based on the weight of the cellulose acetate-butyrate, of resacetophenone.

3. A cellulose acetate-butyrate plastic comprising cellulose acetate-butyrate and, as an agent for inhibiting deterioration of the plastic by ultraviolet light, approximately 1%-2%, based on the weight of the cellulose acetate-butyrate, of res- LESTER W. A. MEYER. WILLIAM M. GEARI-IART. 

